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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:36:03 UTC
Update Date2022-03-07 02:54:56 UTC
HMDB IDHMDB0036459
Secondary Accession Numbers
  • HMDB36459
Metabolite Identification
Common NameMacelignan
DescriptionMacelignan belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Macelignan has been detected, but not quantified in, herbs and spices. This could make macelignan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Macelignan.
Structure
Data?1563862879
Synonyms
ValueSource
AnwulignanHMDB
CalophynHMDB
Chemical FormulaC20H24O4
Average Molecular Weight328.4022
Monoisotopic Molecular Weight328.167459256
IUPAC Name4-[3-(2H-1,3-benzodioxol-5-ylmethyl)-2-methylbutyl]-2-methoxyphenol
Traditional Namemacelignan
CAS Registry Number107534-93-0
SMILES
COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1
InChI Identifier
InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3
InChI KeyQDDILOVMGWUNGD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassDibenzylbutane lignans
Sub ClassNot Available
Direct ParentDibenzylbutane lignans
Alternative Parents
Substituents
  • Dibenzylbutane lignan skeleton
  • Methoxyphenol
  • Benzodioxole
  • Phenylpropane
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Acetal
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point70 - 72 °CNot Available
Boiling Point467.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.067 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.220 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP4.86ALOGPS
logP5.13ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability36.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.19331661259
DarkChem[M-H]-181.61231661259
DeepCCS[M+H]+185.94430932474
DeepCCS[M-H]-183.39430932474
DeepCCS[M-2H]-218.08430932474
DeepCCS[M+Na]+194.37430932474
AllCCS[M+H]+180.732859911
AllCCS[M+H-H2O]+177.232859911
AllCCS[M+NH4]+183.832859911
AllCCS[M+Na]+184.732859911
AllCCS[M-H]-185.632859911
AllCCS[M+Na-2H]-185.532859911
AllCCS[M+HCOO]-185.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.8.54 minutes32390414
Predicted by Siyang on May 30, 202219.0921 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20220.9 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid30.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2744.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid541.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid230.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid257.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid359.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1008.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid889.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)95.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1804.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid717.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1879.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid559.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid529.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate350.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA362.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water8.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MacelignanCOC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C13497.0Standard polar33892256
MacelignanCOC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C12551.2Standard non polar33892256
MacelignanCOC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C12667.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Macelignan,1TMS,isomer #1COC1=CC(CC(C)C(C)CC2=CC=C3OCOC3=C2)=CC=C1O[Si](C)(C)C2731.6Semi standard non polar33892256
Macelignan,1TBDMS,isomer #1COC1=CC(CC(C)C(C)CC2=CC=C3OCOC3=C2)=CC=C1O[Si](C)(C)C(C)(C)C3000.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Macelignan GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-0901000000-22bfca8f123cc67d052f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macelignan GC-MS (1 TMS) - 70eV, Positivesplash10-000i-1955000000-db8e56fb66b08c29ae2c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macelignan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Macelignan , positive-QTOFsplash10-000i-0900000000-d8bdc4c1e4a630ae1fe42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Macelignan , positive-QTOFsplash10-000i-0910000000-c90b1f74544adb5ae68d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOFsplash10-004i-0329000000-956206a54fffd039a2212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOFsplash10-08ic-1942000000-026059a678a1532f8b122016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOFsplash10-0i09-5921000000-e058d00c237d34bd53632016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOFsplash10-004i-0009000000-600c1a450b0ced22ebc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOFsplash10-004i-0039000000-7002ffddbbdf0a7f195c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOFsplash10-0bu0-1392000000-0f40cab6ee1e5be055f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOFsplash10-004i-0009000000-fd417bc7f7b273e091542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOFsplash10-004i-0169000000-751be5e231bc8180cb862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOFsplash10-004i-0549000000-d0aaa2726ea7c14d5c052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOFsplash10-004j-0296000000-78591524d90c87ba316b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOFsplash10-052u-0941000000-dccc0af62bd2f1f9ee0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOFsplash10-0570-0972000000-b1112c488d3d6031c0692021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015348
KNApSAcK IDC00031992
Chemspider ID22370206
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMacelignan
METLIN IDNot Available
PubChem Compound13844304
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1684861
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sohn JH, Han KL, Kim JH, Rukayadi Y, Hwang JK: Protective Effects of macelignan on cisplatin-induced hepatotoxicity is associated with JNK activation. Biol Pharm Bull. 2008 Feb;31(2):273-7. [PubMed:18239286 ]
  2. Ma J, Hwang YK, Cho WH, Han SH, Hwang JK, Han JS: Macelignan attenuates activations of mitogen-activated protein kinases and nuclear factor kappa B induced by lipopolysaccharide in microglial cells. Biol Pharm Bull. 2009 Jun;32(6):1085-90. [PubMed:19483320 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .